# Day Trips from Siena: Val d'Orcia, Crete & Hill Towns

> The best day trips from Siena: Pienza, Montalcino, Montepulciano, the Crete Senesi, Monte Oliveto, San Galgano, San Gimignano and Monteriggioni.

Source: https://villavacations.com/travel-guide/day-trips-from-siena/

Travel Guide · Day Trip Ideas

# Day Trips from Siena: Val d’Orcia, the Crete Senesi and the Towers of San Gimignano

Cypress-lined roads, Renaissance hill towns, a roofless abbey and a village built around a thermal pool, all within an hour of Siena.

[Day Trip Ideas](https://villavacations.com/category/day-trip-ideas/)

By [Susan Russo](https://villavacations.com/author/susan-russo1gmail-com/) · October 28, 2026

![Day Trips from Siena: Val d’Orcia, the Crete Senesi and the Towers of San Gimignano](https://villavacations.com/wp-content/uploads/2026/06/destination-hero-siena.webp)

The best day trips from Siena are the Val d’Orcia, with Pienza, Montalcino and [Montepulciano](https://villavacations.com/destinations/siena/), about an hour south; the [Crete Senesi](https://villavacations.com/destinations/siena/) and the abbey of Monte Oliveto Maggiore, 25 to 40 minutes southeast; [San Gimignano](https://villavacations.com/destinations/siena/), 45 minutes northwest; Monteriggioni, 20 minutes north; the roofless abbey of San Galgano, 40 minutes southwest; and the [Chianti](https://villavacations.com/destinations/chianti/) wine villages, 20 to 40 minutes north. A car or a private driver is the easiest way to see them.

Siena sits at the center of the most photographed countryside in Italy. Drive an hour in any direction and you reach Renaissance hill towns, famous wine villages, a roofless abbey open to the sky and a village built around a steaming thermal pool. Here are the day trips from Siena we plan most often for our clients, with drive times from the city. Most villas near Siena are even closer to one side or the other.

## What can you see in the Crete Senesi?

**The road to Asciano (25 minutes).** Southeast of Siena, the land turns into the *Crete Senesi*, soft clay hills that are green in spring, golden in summer and bare and silvery in the fall, with a lone cypress or farmhouse on every ridge. The road from Siena to Asciano is one of the most beautiful drives in [Tuscany](https://villavacations.com/destinations/tuscany/). Go in the early morning or at sunset, and stop wherever you like.

**Monte Oliveto Maggiore (40 minutes).** A great brick abbey in a cypress wood, still home to Benedictine monks. Its cloister is painted with a cycle of frescoes of the life of Saint Benedict by Luca Signorelli and Sodoma, full of lively detail. The monks also sell their own wine, oil and honey.

**San Giovanni d’Asso (45 minutes).** A small castle village famous for white truffles. In November it holds its truffle fair, and year-round you can join a truffle hunter and their dog in the woods, a highlight for children.

## Is the Val d’Orcia worth a day trip from Siena?

The Val d’Orcia, a UNESCO World Heritage landscape, is the Tuscany of postcards: winding white roads lined with cypresses, wheat fields and hill towns of honey-colored stone. Give it a full day, or two.

**Montalcino (45 minutes).** A walled hill town crowned by a 14th-century fortress, and home to Brunello, one of Italy’s greatest wines. Taste in town or at a winery among the vines, and visit the Romanesque abbey of **Sant’Antimo**, ten minutes below, standing alone among olive trees.

**Pienza (1 hour).** Pope Pius II rebuilt his home village in the 1460s as an ideal Renaissance town, and it remains perfect in miniature. Walk the panoramic lane along the town walls, taste pecorino in the cheese shops on the main street and stay for sunset over the valley.

**Montepulciano (1 hour).** A long, steep hill town of palaces and churches, with wine cellars carved deep into the rock beneath its streets, where you can taste Vino Nobile. The church of San Biagio, below the town, is one of the finest Renaissance buildings in Tuscany.

**Bagno Vignoni and San Quirico d’Orcia (1 hour).** In Bagno Vignoni, the village square is a large pool of steaming thermal water, used since Roman times. You cannot bathe in the square, but there are pools nearby for that. Nearby San Quirico has the lovely Horti Leonini garden and the much-photographed cypress groves on the road toward Pienza. For more warm water, read [the best thermal springs in Tuscany](https://villavacations.com/travel-guide/best-thermal-spring-tuscany/).

Staying in the south puts the Val d’Orcia and the Crete Senesi at your doorstep:

| Villa | Bedrooms / sleeps | Rate | Why we chose it |
| --- | --- | --- | --- |
| [Villa Cardinale](https://villavacations.com/villas/villa-cardinale/) Siena | 8 / 16 | From €32,000 / week | Near Buonconvento, about 20 minutes from Montalcino |
| [Villa Aiola](https://villavacations.com/villas/villa-aiola/) Siena | 6 / 12 | From €12,145 / week | Woodland trails and Val d'Orcia views from the pool |
| [Villa Araldica](https://villavacations.com/villas/villa-araldica/) Siena | 7 / 12 | From €14,450 / week | An 18th-century villa in 60 acres of parkland near Montepulciano |
| [Villa Benessere](https://villavacations.com/villas/villa-benessere/) Siena | 10 / 20 | From €21,191 / week | Between the Val di Chiana and the Val d'Orcia, with a wellness annex |

## What is the sword in the stone at San Galgano?

**The Abbey of San Galgano (40 minutes).** A vast Cistercian abbey whose roof fell in centuries ago, leaving soaring stone arches open to the sky and grass for a floor. On the hill above, the round chapel of Montesiepi holds a medieval sword driven into a rock, Tuscany’s own sword in the stone. Bring a picnic.

## Which hill towns are closest to Siena?

**Monteriggioni (20 minutes).** A tiny village inside a perfect ring of walls and towers, mentioned by Dante. Walk the ramparts, have lunch in the little piazza and look out over the Via Francigena, the pilgrim road to [Rome](https://villavacations.com/destinations/rome/). In early July, a medieval festival fills the village.

**San Gimignano (45 minutes).** The town of towers: fourteen still stand of the dozens that once rose over the town. Climb the Torre Grossa for the view, see the frescoes in the Collegiata and taste the white Vernaccia. It is busy at midday, so go early in the morning or come for dinner, when the day visitors have gone.

**Colle di Val d’Elsa (25 minutes).** A handsome, less-visited hill town known for its crystal workshops, with a long upper town built along a ridge. [Villa Collina](https://villavacations.com/villas/villa-collina/) is close by.

**Volterra (1 hour 15 minutes).** A stern, beautiful Etruscan and medieval town on a high ridge, famous for alabaster carving and an excellent Etruscan museum.

## How do you visit Chianti from Siena?

The [Chianti Classico](https://villavacations.com/destinations/chianti/) wine country begins 20 minutes north of Siena. Follow the scenic SR222 road through Castellina, Panzano and Greve, or wander east to Radda, Gaiole and the castle of Brolio, where the formula for Chianti was first written down. Our [day trip ideas from Chianti](https://villavacations.com/travel-guide/chianti-day-trip-ideas/) and our guide to [wine country near Siena](https://villavacations.com/travel-guide/wine-country-near-siena/) have more.

Private tours with Context Travel

Let someone else drive

A full day in the Val d'Orcia and the Crete Senesi with a historian and a driver, or San Gimignano's towers and Volterra's Etruscan treasures in one trip west of Siena.

![Full-Day Tuscany Day Trip from Siena with Wine Tasting](https://villavacations.com/wp-content/uploads/2026/06/eod-context-siena-day-in-val-d.jpg)

From

$582

per person

Full day · private · tastings included

### Full-Day Tuscany Day Trip from Siena with Wine Tasting

Pienza, Montepulciano, the cypress road outside San Quirico, the abbey at Monte Oliveto Maggiore. The full Crete Senesi day with a local driver and a historian.

Private, priced per group: $2,572 for 2, about $582 per person for 6.

Book this experience

![Full-Day San Gimignano and Volterra Day Trip from Siena](https://villavacations.com/wp-content/uploads/2026/06/eod-context-siena-full-day-san-gimignano.jpg)

From

$543

per person

Full day · private

### Full-Day San Gimignano and Volterra Day Trip from Siena

San Gimignano's towers, Volterra's Etruscan museum and alabaster workshops. The medieval-Etruscan double bill of the Tuscan hills west of Siena.

Private, priced per group: $2,494 for 2, about $543 per person for 6.

Book this experience

[See all 5 private tours in Siena →](https://villavacations.com/experiences/siena/)

## Do you need a car for day trips from Siena?

Buses connect Siena with the bigger towns, but the beauty of this countryside is in the roads between them, so a car or a private driver is the way to go. Wine tasting days are best with a driver; several of our villas can arrange one. Watch for limited traffic zones (ZTL) in every historic center, and park outside the walls.

## Plan your days with us

The right villa makes every day trip shorter. Read [where to stay in Siena](https://villavacations.com/travel-guide/where-to-stay-in-siena/), browse our [villas near Siena](https://villavacations.com/destinations/siena/), or [talk to a Doorways advisor](https://villavacations.com/contact-us/) and we will plan your week around what you love.

## More from our Siena guides

- [Where to Stay in Siena: Inside the Walls or a Villa in the Hills](https://villavacations.com/travel-guide/where-to-stay-in-siena/)
- [The Best Time to Visit Siena, Month by Month](https://villavacations.com/travel-guide/best-time-to-visit-siena/)
- [The Palio di Siena Explained: The Race, the Contrade and How to See It](https://villavacations.com/travel-guide/palio-di-siena/)
- [What to Eat in Siena, From Pici to Panforte](https://villavacations.com/travel-guide/what-to-eat-in-siena/)
- [Wine Country Near Siena: Chianti Classico, Brunello and Vino Nobile](https://villavacations.com/travel-guide/wine-country-near-siena/)
- [Siena vs. Florence vs. San Gimignano: How Many Days, and Where to Base Yourself](https://villavacations.com/travel-guide/siena-vs-florence-vs-san-gimignano/)
- [Day Trip Ideas from Chianti](https://villavacations.com/travel-guide/chianti-day-trip-ideas/)
- [Large Villas in Chianti and Siena for 16 or More Guests](https://villavacations.com/travel-guide/large-villas-chianti-siena-16-guests/)
- [Siena villas and destination guide](https://villavacations.com/destinations/siena/)

## Frequently asked questions

**What is the best day trip from Siena?**

The Val d'Orcia, a UNESCO World Heritage landscape about an hour south, is our favorite: Pienza for pecorino, Montalcino for Brunello and the cypress-lined roads in between.

**How far is San Gimignano from Siena?**

About 45 minutes by car. Visit early in the morning or stay for dinner, when the day visitors have gone.

**Do you need a car for day trips from Siena?**

Buses reach the bigger towns, but a car or a private driver is the only practical way to see the Crete Senesi and the Val d'Orcia, where the beauty is in the roads between the towns.

**Can you visit the Cinque Terre on a day trip from Siena?**

It is possible but long: about three hours each way by car. We suggest spending a night or two on the coast instead, and keeping your Siena days for the Val d'Orcia, Chianti and San Gimignano.

**How far is Montepulciano from Siena?**

About an hour by car, through the Crete Senesi or the Val di Chiana. Pienza is about the same, and the two make a perfect day together.

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## Hand-selected villas in *Siena*

![Villa Hortus](https://villavacations.com/wp-content/uploads/2026/06/villa-hortus-01-20191014_125947jpg-1024x682.jpg)

Siena

### Villa Hortus

5 Beds·5 Baths·10 Guests

![Villa Aiola](https://villavacations.com/wp-content/uploads/2026/06/villa-aiola-01-20181205_112122jpg-1024x682.jpg)

Siena

### Villa Aiola

6 Beds·5 Baths·12 Guests

![Villa Araldica](https://villavacations.com/wp-content/uploads/2026/06/villa-araldica-01-20251023_095757_1832jpg-1024x682.jpg)

Siena

### Villa Araldica

7 Beds·7 Baths·12 Guests

[Browse All Villas](https://villavacations.com/villas/?destination=Siena)

About the author

### Susan Russo

Susan Russo is the owner of Doorways Villa Vacations, which is focused on offering hand-selected luxury villas in the most sought-after Italian destinations.

As a dual citizen of Italy and the US, she loves visiting Italy often and scouting unique locations and experiences to share La Dolce Vita with her clients.

Travel Guide

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